1. Field of the Invention:
The present invention relates to a process for producing 1,3,5-triaminobenzene by reacting ammonia with 3,5-diaminochlorobenzene in the presence of a copper compound catalyst.
2. Description of the Prior Art:
1,3,5-Triaminobenzene which has amino radicals at 1,3 and 5-positions on benzene nuclear is an important source in industrial organic syntheses. It has been difficult to produce 1,3,5-triaminobenzene in an industrial process. It has been known to produce 1,3,5-triaminobenzene by the following processes.
(1) The process for reducing 1,3,5-trinitrobenzene obtained by using 2,4,6-trinitrotoluene as a source (Chemical Abstract Vol. 62, 9047 e(1965).
(2) The process for reducing 2,4,6-trinitrochlorobenzene obtained by using 2,4,6-trinitrophenol as a source (Yuki Kagobutsu Gosei Ho Vol. 9 page 87-88 edited by Yuki Gosei Kagaku Kyokai). These processes are disadvantageous as an industrial process because explosive nitrobenzenes are used or complicated reaction steps are needed.
On the other hand, the process for producing 3,5-dichloroaniline or 3,5-diaminochhlorobenzene by an amination of 1,3,5-trichlorobenzene has been disclosed (Yuki Gosei Kagaku Vol. 36 No. 9 (1978) page 784-788). The process for producing 3,5-dichloroaniline by an amination of 1-bromo-3,5-dichhlorobenzene has been disclosed (Japanese Unexamined Patent Publication No. 633 23/1978). In these references, there is not any disclosure of a production of 1,3,5-triaminobenzene.
If it is possible to produce directly 1,3,5-triaminobenzene by an amination of sym-trihalogenobenzene, the disadvantages of the conventional processes can be overcome. This is remarkably advantageous however, such desired reaction is not performed. This fact is confirmed by the description of Yuki Gosei Kagaku that in the amination of 1,3,5-trichlorobenzene in the presence of a copper type catalyst, 3,5-dichloroaniline is produced at a ratio of 30 to 40% and also m-dichlorobenzene as a by-product is produced at a ratio of 60 to 70% by a dechlorination.